Ethanolamine → 2-((1-Phenylethyl)amino)ethan-1-ol

A mixture of acetophenone (2.00 g, 16.6 mmol, Eq: 1.00), 2-aminoethanol (3.05 g, 49.9 mmol, Eq: 3.00) and titanium(IV) isopropoxide (6.15 g, 6.41 ml, 21.6 mmol, Eq: 1.3) in absolute methanol (25 ml) was stirred under nitrogen at room temperature for 48 hrs. Sodium borohydride (630 mg, 16.6 mmol, Eq: 1.00) was then added at 0° C. and the resulting mixture was stirred for an additional 2 hr. The reaction was then quenched by adding water (1 ml). Stirring was continued at room temperature for 20 min., then the reaction mixture was acidified with 1N HCl. After filtration over a pad of Celite, washing with ethyl acetate, any drying over magnesium sulfate, the mixture was concentrated to obtain 2-(1-phenylethylamino)ethanol (oil, 2.71 g, 16.4 mmol, 98.5% yield).

1. stirringthe resulting mixture was stirred for an additional 2 hr
2. customThe reaction was then quenched
3. additionby adding water (1 ml)
4. stirringStirring
5. waitwas continued at room temperature for 20 min.
6. filtrationAfter filtration over a pad of Celite
7. washwashing with ethyl acetate
8. concentrationany drying over magnesium sulfate, the mixture was concentrated

ORD record

ord-49c0fc5cdae94206983e1cb1ba8d94cd

Source dataset

uspto-grants-2015_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09045486B2